1,6-Dibromohexane → HCID 23045257, compound

HRID 2108138Notes

Reaction equation

HRID 2108138 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][S:9][CH2:10][CH2:11][OH:12].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[OH-].[Na+]>O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:12][CH2:11][CH2:10][S:9][CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 234225272-{[2-(2-Pyridinyl)ethyl]thio}ethanol

Product 1

HCID 23045257HCID 23045257, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[[2-(2-pyridinyl)ethyl]thio]ethanol (0.50 g), 1,6-dibromohexane (2.13 g), TAB (0.4 g) and 50% aqueous sodium hydroxide (6 ml) was stirred under nitrogen for 6 h, then diluted with water (75 ml) and extracted with diethyl ether (2×150 ml). The organic extracts were evaporated in vacuo to give an oil, which was partitioned between 2N hydrochloric acid (100 ml) and hexane (2×100 ml). The aqueous phase was basified to pH 12 with 50% aqueous sodium hydroxide and extracted with diethyl ether (2×150 ml), the dried organic extracts were evaporated in vacuo to give an oil. Purification by FCC eluting with System F (1:1) gave the title compound (0.60 g) as a colourless oil. T.l.c. (diethyl ether) Rf 0.64

Workup

  1. extractionextracted with diethyl ether (2×150 ml)
  2. customThe organic extracts were evaporated in vacuo
  3. customto give an oil, which
  4. customwas partitioned between 2N hydrochloric acid (100 ml) and hexane (2×100 ml)
  5. extractionextracted with diethyl ether (2×150 ml)
  6. customthe dried organic extracts were evaporated in vacuo
  7. customto give an oil
  8. customPurification by FCC
  9. washeluting with System F (1:1)

Sources & evidence

ORD record
ord-4a20ad5028044648ab25d1acb0dbc34c
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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